Citation: Ye Qian Wen, Wei Min Ren, Xiao Bing Lu. Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN[J]. Chinese Chemical Letters, ;2011, 22(11): 1285-1288. doi: 10.1016/j.cclet.2011.06.016 shu

Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Received Date: 15 March 2011

Fund Project: This work was support by a Foundation for the Author of National Excellent Doctoral Dissertation of China (No.FANEDD, 200759).

A novel enantiopure salen ligand bearing a diphenylphosphine oxide on the 3-position of one aromatic ring was synthesized and combined with Ti(Oi-Pr)₄ as a monometallic bifunctional catalyst for asymmetric cyanosilylation reaction of aldehydes with trimethylsilyl cyanide (TMSCN). The catalyst system exhibited excellent activity and moderate enantioselectivity. The addition of TMSCN to 4-nitrobenzaldehyde in the presence of 1 mol% catalyst loading could complete within 10 min at ambient temperature. An intramolecularly cooperative catalysis was observed in this system wherein the central metal Ti(IV) is suggested to play a role of Lewis acid to activate aldehydes while the appended diphenylphosphine oxide worked as Lewis base to activate TMSCN.
- Cyanohydrin,
- Bifunctional catalyst,
- Salen,
- TMSCN,
- Diphenylphosphine oxide
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